5-(4-Nitrophenyl)-1,3-oxazole → 4-(1,3-Oxazol-5-yl)aniline

HRID 28583

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][CH:13]=[N:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C.CO.[Fe]>[O:14]1[C:10]([C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)=[CH:11][N:12]=[CH:13]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 5-(4-nitro-phenyl)-oxazole (2.0 g, 10.5 mmol), iron powder (2.4 g, 42.8 mmol) in acetic acid (5 ml) and methanol (30 ml) was stirred at 60° C. for 1 hour. After filtration through a pad of celite under suction, the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (3:4 followed by 3:2) to give 4-oxazol-5-yl-phenyl-amine (1.4 g, 83% yield). 1H NMR (acetone-d6) δ 5.0 (br s, 2H, NH), 6.76 (d, 2H, J=8.7 Hz, Ar), 7.12 (s, 1H, Ar), 7.45 (d, 2H, J=8.6 Hz, Ar), 8.04 (s, 1H, Ar).

Workup

filtrationAfter filtration through a pad of celite under suction
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by flash chromatography
washeluting with ethyl acetate-hexane (3:4 followed by 3:2)

Sources & evidence

ORD record: ord-6f1e12607b364e42a2848d5e70461bf3
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419984B2

Linked notes

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